germanicopolitana, S.brevidens, and the Seed Bank of the Aegean Agricultural Institute, MenemenâIzmir, for seeds of S. athoa. REFERENCES. 1. P. H. Davis ...
Chemistry of Natural Compounds, Vol. 37, No. 4, 2001
FATTY ACID COMPOSITION OF Sideritis SPECIES*
A. Ertan,1,2 N. Azcan,2,3 B. Demirci,1,2 and K. H. C. Baser1,2
UDC 547.915:665.33
Seed oils of 15 Sideritis species collected from different regions in Turkey (S. athoa, S. brevidens, S. caesarea, S. condensata, S. congesta, S. dichotoma, S. erythrantha var. cedretorum, S. germanicopolitana ssp. germanicopolitana, S. hololeuca, S. lanata, S. libanotica ssp. violascens, S. lycia, S. niveotomentosa, S. perfoliata, S. phrygia, S. pisidica) were obtained by a Soxhlet apparatus using hexane. The oil yields were found to be between 5.6–36.3%. Fatty acids in the oils were converted to methyl esters and their compositions were determined by GC/MS. The main fatty acid components of the oils from all the species are linoleic (45.4–64.0%), oleic (12.3–26.5%), 6-octadecynoic (4.5–26.8%), palmitic (0.3–9.4%), and linolenic (0.8–2.0%) acids. Key words: Lamiaceae, Sideritis athoa, S. brevidens, S. caesarea, S. condensata, S. congesta, S. dichotoma, S. erythrantha var. cedretorum, S. germanicopolitana ssp. germanicopolitana, S. lanata, S. libanotica ssp. violascens, S. lycia, S. niveotomentosa, S. perfoliata, S. phrygia, S. pisidica, seed oil, fatty acid, linoleic acid, oleic acid, linolenic acid. The genus Sideritis (Lamiaceae-subfamily Lamioideae) is represented by 46 species and 53 taxa in Turkey, 39 taxa being endemic (78.2%). Sideritis species are widely used as herbal tea and folk medicine in Turkey. These species are known to have antiinflammatory, antispasmodic, carminative, analgesic nervous system stimulant, sedative, antitussive, stomachic, anticonvulsant, and antifeedant activities [1–4]. Most of the studies on Sideritis species comprise their essential oils and flovanoids. There is no work on the seed oils of Sideritis. Here, we report on the seed oil compositions of 15 Sideritis species (S. athoa papanikolaou and Kokkini., S. brevidens P.H. Davis, S. caesarea Duman, Aytac and Baser, S.condensate Boiss. and Heldr. Apud Bentham, S. congesta P.H. Davis Hub.Mor., S. dichotoma Huter., S. erythrantha Boiss. var. cedretorum , S. germanicopolitana Boiss ssp. germanicopolitana, S. lanata L., S. libanotica Labill. ssp. violascens, S. lycia Boiss. and Heldr., S. niveotomentosa Hub.-Mor., S. perfoliata L., S. phrygia Bornm., S. pisidica Boiss. and Helder.). Seeds were collected from Sideritis species growing in different localities in Turkey, and the oil yields of the seeds were found to be between 5.6–36.3% in 15 Sideritis species investigated (Table 1). The fatty acid compositions of the oils are summarized in Table 2. The dominant fatty acid in all the species was linoleic acid. Its content ranged from 45.4 to 64.0%. Oleic acid was less abundant (12.3–26.5%) (Table 2). While oleic acid was found to be the second major fatty acid component of most species, 6octadecynoic acid (26.8%), an unusual fatty acid, was present as the second main component in the oil of S. pisidica and in significant quantity in the oil of S. caesarea (12.9%). The U/S (Unsaturated/Saturated; 4.4–18.3) index, also presented in Table 2, which was considered as a taxonomic marker, does not appear to have much significance in the taxonomy of the family Lamiaceae [5, 6]. ______ *Presented at the 4th International Symposium on the Chemistry of Natural Compound (SCNC), 6-8 June 2001, Isparta, Turkey. 1) Faculty of Pharmacy, Department of Pharmacognosy, Anadolu University; 2) Medicinal and Aromatic Plant and Drug Research Centre (TBAM), Anadolu University; 3) Engineering and Architecture Faculty, Department of Chemical Engineering, Anadolu University, 26470, Eskisehir, Turkey. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 259-261, May-June, 2001. Original article submitted June 19, 2001. 0009-3130/01/3704-0301$25.00 © 2001 Plenum Publishing Corporation
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TABLE 1.Collection Sites and Seed Oil Yields of Sideritis Species Species S. athoa S. niveotomentosa S. perfoliata S. phrygia S. pisidica S. congesta S. germanicopolitana ssp. germanicopolitana S. brevidens S. caesarea S. libanotica ssp. violascens S. lycia S. erythrantha var. cedretorum S. lanata S. dichotoma S. condensata
Collected Area
Oil Yield, %
Balikesir, Edremit, Mehmetalan Village to Kazdagi 9-10 km Icel-Mut-Culnar Road Alanya Afyon-Cay-Sultan Mountain Antalya-Termesos Isparta-Egirdir-Akpinar Village Kirsehir-Karaman-Savcili, Kostepe
25.0 28.0 25.6 5.6 9.0 29.6 27.0
Icel-Mut-Gulnar Kayseri-Sariz Antalya Antalya-Kemer Antalya-Alanya Aydin-Narliova Balikesir-Edremit-Kazdagi-Ortaoba Antalya-Manavgat-Yukari Isiklar Village
24.0 35.4 36.3 18.0 20.0 25.0 20.0 19.5
TABLE 2. Fatty Acid Compositions of Sideritis Species, % Fatty Acids
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
8:0 9:0 12:0 14:0 15:0 16:0 16:1(7Z) 16:1(9Z) 16:2(9,12) 17:0 18:0 18:1(9Z) 18:1(9E) 18:2 18:1(6 yn)* 18:3 20:0 20:1 22:0 24:0 Total ΣSaturated ΣUnsaturated U/S 18:3/18:2
Tr. Tr. Tr. 6.0 0.1 0.1 0.1 2.8 25.4 1.2 54.6 4.5 1.3 0.2 0.5 95.3 9.1 86.2 9.5 0.02
Tr. Tr. 0.1 Tr. 6.9 0.1 0.1 Tr. 0.1 3.3 24.8 1.1 52.6 7.6 1.2 0.1 0.6 0.1 98.7 12.3 86.4 7.0 0.02
Tr. Tr. 0.1 Tr. 7.0 0.1 0.1 0.1 4.0 24.5 1.2 56.1 5.3 0.9 0.1 0.3 Tr. Tr. 99.8 11.3 88.5 7.8 0.02
Tr. Tr. Tr. 0.1 Tr. 5.7 0.1 0.1 0.1 3.0 25.0 0.9 52.9 7.0 1.3 0.2 0.6 0.2 0.2 96.5 9.3 87.2 9.4 0.03
Tr. 0.2 0.2 8.9 Tr. Tr. 0.1 2.4 12.3 0.8 45.4 26.8 2.0 0.1 Tr. 99.2 11.9 87.3 7.3 0.04
Tr. Tr. 0.1 Tr. 7.0 0.1 0.1 0.1 3.1 25.9 1.1 53.8 6.1 1.3 0.1 0.5 Tr. Tr. 99.3 10.4 88.9 8.5 0.02
Tr. Tr. 0.1 Tr. 5.1 Tr. 0.1 2.3 19.4 0.9 64.0 5.9 0.8 0.1 0.5 99.2 7.6 91.6 12.1 0.01
Tr. Tr. Tr. 0.3 0.1 0.1 4.1 26.5 1.1 52.3 4.9 1.2 0.2 Tr. 90.8 4.7 86.1 18.3 0.02
Tr. Tr. Tr. 0.1 0.1 6.6 0.2 0.1 0.1 2.4 18.5 0.9 55.0 12.9 1.6 0.1 0.5 Tr. 99.1 9.4 89.7 9.5 0.03
Tr. Tr. Tr. 0.1 Tr. 8.0 0.1 0.1 0.1 2.5 21.3 1.3 53.6 9.1 1.6 0.1 0.7 0.1 Tr. 98.7 10.9 87.8 8.1 0.03
Tr. 0.2 2.6 0.7 0.1 9.4 0.2 0.3 Tr. 0.1 4.9 20.3 1.0 48.9 8.4 1.0 0.2 0.3 0.1 Tr. 98.7 18.3 80.4 4.4 0.02
0.1 Tr. 0.1 0.1 8.7 0.1 Tr. 0.1 3.6 21.6 0.8 54.2 8.6 1.4 0.1 Tr. 99.5 12.8 86.7 6.8 0.03
Tr. Tr. Tr. 0.1 Tr. 8.2 0.1 0.1 0.1 3.2 22.9 0.8 49.7 11.5 1.3 0.2 0.2 0.1 Tr. 98.5 11.9 86.6 7.3 0.03
Tr. 0.1 0.1 0.2 0.1 7.1 0.3 0.1 0.1 2.5 22.4 0.8 57.0 7.3 1.4 Tr. Tr. 99.5 10.2 89.3 8.8 0.03
Tr. Tr. 0.1 Tr. 0.1 6.9 0.2 0.1 0.1 3.8 19.6 0.8 56.2 8.1 1.1 0.1 0.4 Tr. 97.6 11.1 86.5 7.8 0.02
______ 1 - S. athoa, 2 - S. niveotomentosa, 3 - S. perfoliata, 4 - S. phrygia, 5 - S. pisidica, 6 - S. congesta, 7 - S. germanicopolitana ssp. germanicopolitana, 8 - S. brevidens, 9 - S. caesarea, 10 - S. libanotica ssp. violascens, 11 - S. lycia, 12 - S. erythrantha var. cedretorum, 13 - S. lanata, 14 - S. dichotoma, 15 - S. condensata. Tr: Trace, lower than 0.1. U/S: Unsaturated/Saturated. *Tentative identification by GC/MS.
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TABLE 3. GC/MS Analysis Conditions System
Hewlett Packard GCD
Column
Innowax (60 m × 0.25 1, 0.25 m film thickness) fused silica capillary column Helium, 1 ml/min 250oC 60oC for 10 min, 220oC at a rate of 4oC/min and kept constant at 220oC for 10 min, 240oC at a rate of 1oC/min 50:1 70 eV 35-425 m/z
Carrier gas and flow rate Injection temperature Column temperature Split ratio Electron ehergy Mass range
According to Maffei et al. fatty acids were mainly composed of 18:3 in leaves and flowers of Lamiaceae [6]. Its findings reflect, in part, previous reports on fatty acid composition of seed lipids in the family Lamiaceae . In the seed oils of the genus Sideritis 18:2 was found to be the main component. The main fatty acid components vary between the two subfamilies of Lamiaceae, namely Lamioideae and Nepetoideae [7]. In the subfamily Lamioideae, the ratio of 18:3 fatty acid is less than 30%, and in most species it is even less than 5%. Since Sideritis belongs to this subfamily, our results agree with these findings in that it is 0.01–0.04. Likewise, the ratio of 18:3/18:2 ranged between 0.01–0.04, in agreement with the characteristics of the subfamily Lamioideae.
EXPERIMENTAL Fifteen Sideritis species were collected from different regions of Turkey (Table 1). Seeds were separated from plant material. The amount of seeds from each species varied between 0.03 and 2.5 g. Seed oil was obtained using a 25 ml capacity Soxhlet apparatus with n-hexane, and fatty acids were later converted to methyl esters with 14% BF3 in methanol [8]. The fatty acid compositions of the seed oils were determined by GC/MS and its conditions are given in Table 3. We would like to thank Prof. Dr. Mecit Vural for supplying the seeds of S. germanicopolitana ssp., germanicopolitana, S.brevidens, and the Seed Bank of the Aegean Agricultural Institute, Menemen–Izmir, for seeds of S. athoa.
REFERENCES 1. 2. 3. 4. 5. 6. 7. 8.
P. H. Davis, Flora of Turkey and East Aegean Islands, 10, University Press, Edinburgh, 1988, 203. N. Kirimer, N. Tabanca, G. Tumen, H. Duman, and K.H.C. Baser, Flav. Frag. J., 14, 421 (1999). A. Godoy, B. Heras, J. M. Vivas, and A. Villar, Biol. Pharm. Bull., 23, 1193 (2000). M. L. Bondi, M. Bruno, F. Piozzi, K. H. C. Baser, and M. S. J. Simmond, Bio. Chem. Syst. Ecol., 28, 299 (2000). P. D. Marin, V. Sajdl, S. Kapor, B. Tatic, and B.Petkovic, Phytochemistry, 30, 2979 (1991). M. Maffei, and S. Scannerini, Bio. Chem. Syst. Ecol., 21, 475 (1993). P. D. Cantino, and R.W. Sander, Syst. Bot., 11, 163 (1986). S. Williams, Official Methods of Analysis of the Association of Official Analytical Chemists, Virginia, USA, 1984, 503.
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